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<h1><a href="https://archiveofourown.org/works/28293630">HBO Dean</a> by <a class='authorlink' href='https://archiveofourown.org/users/WarriorQean/pseuds/WarriorQean'>WarriorQean</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Supernatural</td></tr>

<tr><td><b>Genre:</b></td><td>Big Gay Love Story, Bisexual Dean Winchester, Friendship, Homophobic John Winchester, Internalized Homophobia, M/M, Repressed Bisexual Dean Winchester, Supportive Sam Winchester</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-12-24</td></tr>

<tr><td><b>Updated:</b></td><td>2020-12-24</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-11 00:26:53</td></tr>

<tr><td><b>Rating:</b></td><td>Not Rated</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>1,211</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/28293630</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/WarriorQean/pseuds/WarriorQean</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>The story of how a repressed Dean Winchester finds himself, and maybe someone else along the way.</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Castiel/Dean Winchester, Charlie Bradbury &amp; Dean Winchester, DeanCas, Destiel</td></tr>

<tr><td><b>Comments:</b></td><td>2</td></tr>

<tr><td><b>Kudos:</b></td><td>91</td></tr>

</table>

<a name="section0001"><h2>HBO Dean</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>Based on a tumblr post about what Dean would be like if the show was on HBO.</p>
    </blockquote></div><div class="userstuff module">
    
    <p>Dean always knew he liked boys. From the moment Trevor Blocner told him what a crush was in the 3rd grade and said boys pulled the girls hair to let them know they liked them.</p><p>Dean had wished on the spot that Trevor would have pulled his hair instead of Lindsey Lakewood’s.</p><p>The confusing part was that Dean also had a crush on Erin Wilkes. Erin was hot. All the guys said so. They all talked about the things they wanted to do to her in the halls. Dean only wanted to hold her hand, maybe go to the movies or make her a mixtape. But he was a man. Men didn’t do girly things like talk about their feelings. Men never tried on eyeliner or skirts when their dads and brothers weren’t home.</p><p>And as his father instilled on him over and over again:</p><p>“Boys don’t kiss boys.”</p><p>He would use slang like "fucking fag" or "homo" as an insult.</p><p>So Dean went out with Erin. He took her to the movies and for a ride in the Impala his dad had given him for his birthday. He kissed her in the backseat and put his hands up her shirt like he was supposed to.</p><p>He was a man. That didn’t mean he had to like it.</p><p>—-</p><p>The first time Dean heard the word bisexual, he was 24. It had been Sam actually, telling him about this girl he’d talked to the night before. How she had talked girls with him.</p><p>“Wait a minute there Sammy. I thought you slept with this chick.”</p><p>Sam laughed as if it was the most obvious thing in the world, “Yeah Dean, I did.”</p><p>“You just said she was checking out some other chick.”</p><p>“She was bi Dean.”</p><p>“Bi?”</p><p>“Bisexual. She’s attracted to men and women.” Sam picked up a book as of the conversation was over.</p><p>Dean hoped he was hiding his shock well. “You can do that?”</p><p>Now Sam was confused, “Um...yeah.”</p><p>If this girl could like both, maybe Dean could too? </p><p>---</p><p>Charlie was good for him.</p><p>She was someone who his dad would have never approved of. Would have said that she needed to be straightened out or some shit like that. Dean couldn't have given two shits whether the redhead was gay or straight, he loved her all the same.</p><p>Once, they were just hanging out in the bunker watching some movie. Sam had gone to look into a case a few states away. It was nice to just be with Charlie. She never judged him for liking "girly" movies and stuff like his dad had. She never said anything about the lingering glances Dean sometimes gave men when they went out. If anyone had clued in on his preferences it would have been her. </p><p>After the movie they ended up in the bathroom. Dean had made some offhand comment about makeup and now Charlie had insisted she show him a few things about the product. She was currently trying to wrestle some eyeliner or whatever onto his face.</p><p>"Will you just stand still?" She yelled, "It's not that big of a deal Dean!"</p><p>Dean deflected her, "I don't want any black gunk...stick thing anywhere near my eyes."</p><p>Charlie rolled her eyes, "Come onnnnn, it's fun."</p><p>"Yeah for you maybe."</p><p>Charlie gave him a stern look that he knew better than to argue with. She instructed him to close his eyes "softly" whatever that meant and then she carefully applied the eyeliner. After opening and looking in the mirror, Dean was surprised.</p><p>He kind of...liked it.</p><p>The black enhanced his eyes and gave them a slight sparkle. For one fleeting moment he thought about putting it on himself. Applying the gunk in his own mirror carefully before going out. Other people seeing him like this. It sounded so freeing. </p><p>All at once though his father's voice was in his head. Telling him that he was a man. Men didn't go out wearing makeup in public, and Winchester's never even thought about it.</p><p>Dean turned gruffly from the mirror, "Is there something I can take it off with?"</p><p>Charlie looked almost sad for him, "Dean.."</p><p>"Now."</p><p>Reluctantly, she handed him a cloth.</p><p>And if Dean swiped the eyeliner from Charlie's purse when she wasn't looking no one had to know. If he stood in the bathroom late at night when Sam was asleep and tried to mimic the precise motions Charlie had done when swiping the color on and underneath his lids no one had to know. Dean Winchester fought the voice inside his head late at night where no one could see him, and committed one of the many infractions of being a man.</p><p>---</p><p>Cas was...unexpected. </p><p>He smiled at dumb things and was naive enough that anything and everything was magic to him. He was astounded by the toaster. Dean having come into the kitchen one morning with Cas holding a piece of bread over the open flame of the stove. Completely burnt on one end and white as ever on the other.</p><p>Dean had laughed for a good six minutes before he finally addressed Cas about why.</p><p>The stupid angel was endearing and cared too much or not at all.</p><p>Dean loved that about him.</p><p>Scratch that, Dean loved everything about him.</p><p>John's voice was ever present in his head though. Telling him that Winchester's weren't fags, or fairies, or anything other than screw em' once and lose em' men. Yet Dean wanted to kiss Cas every time he smiled. He wanted to hold his hand and wake up in his arms and do all of the cringe-worthy gooey romantic stuff included in rom-coms. Only the voice in his head was loud and persistent, without fail.</p><p>So Dean suffered in his silence. Only allowing Cas to be his best friend, nothing more and never any less.</p><p>---</p><p>Sam had asked to talk to him. Whenever Sam wanted to "talk" it was usually about something he thought was bothering Dean. Usually the thing that was bothering Dean he would push down with beer and sex until the issue was no longer on his mind. He knew it was unhealthy, he just didn't care.</p><p>Sam was fiddling with something in his pocket when Dean stopped baby on a side road. He shifted into park and looked at his brother.</p><p>"Alright Sam, spit it out."</p><p>Sam took a breath and then laid something on the dash. The colors of the charm danced with the sun.</p><p>Dean carefully picked the item up. It had a hook at one end, as if it would be hung from something. A wire was adorned with beads. Beads colored in blue, purple, and pink. </p><p>"Dad's gone Dean." Dean looked at his brother, Sam looked back. "You don't have to be afraid of who you are. Not with me. Not with anyone."</p><p>Dean held the charm for a minute, weighing the voice with what Sam was telling him now. In a split second decision, Dean hung the charm from baby's rearview mirror, and shifted into drive.</p><p>(Dean kissed Cas in the kitchen the next day. The angel laughed and pulled him in while Sam whistled and gave one of his signature "I knew it" smiles).</p>
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